The “motherhood earnings penalty” is a well-established finding in many Western countries. However, a divide between mothers and nonmothers might oversimplify reality given that the family life course has diversified over the last decades. In addition, whether family choices have consequences for women’s employment and earnings in later life is not well known, particularly in a comparative perspective. Using data on 50- to 59-year-old women from the Generations and Gender Programme, the British Household Panel Survey, and SHARELIFE for 22 European countries, we derive a typology of women’s family trajectories and estimate its association with women’s later-life employment and earnings. Whereas family trajectory–related differences with regard to employment were relatively small, our findings reveal a clear, long-lasting family trajectory gradient in earnings. Childless women (with or without a partner) as well as single mothers had higher personal earnings than women whose family trajectories combined parenthood and partnership. Moreover, in societies in which reconciliation of work and family during midlife is less burdensome, labor market outcomes of women following different family trajectories converge. Our findings show that women’s fertility and partnership behavior are inevitably interrelated and jointly influence employment and earning patterns until later in life. The results imply that promoting equal employment opportunities could have long-lasting effects on women’s economic independence.